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MIDA Boronates for Suzuki–Miyaura Cross-Couplings

Professor Martin Burke and coworkers recently prepared retinal using key MIDA building block BB1 in iterative Suzuki-Miyaura cross coupling reactions (Scheme 1). The MIDA unit of BB1 is unreactive under these conditions, allowing for the selective cross-coupling of BB1 with triene (1). Subsequent hydrolysis of the MIDA unit of (2) followed by a second Suzuki-Miyaura reaction provided all-trans-retinal.

Scheme 1: Iterative Suzuki-Miyaura cross-couplings in the synthesis of all-trans-retinal.(703478)

The many advantages of the MIDA boronate platform include air and moisture stability, stability under anhydrous cross-coupling conditions, compatibility with a range of common and harsh reagents, solubility in various organic solvents, silica gel compatibility, and the ability to undergo slow release cross-couplings.